Man2Ac3Ac4Ac6Ac(a1-2)Man3Ac4Ac6Ac(a1-2)Man3Ac4Ac6Ac(a)-O-C(NH)CCl3 | 210295-18-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Man2Ac3Ac4Ac6Ac(a1-2)Man3Ac4Ac6Ac(a1-2)Man3Ac4Ac6Ac(a)-O-C(NH)CCl3
• 英文别名: [(2R,3R,4S,5S,6R)-3,4-diacetyloxy-6-[(2R,3S,4S,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-2-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl]oxy-5-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 210295-18-4
• 化学式: C₄₀H₅₂Cl₃NO₂₆
• 分子量: 1069.2
• InChiKey: XWCCWJDFIUHXQH-DRUXMBDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  70
• 可旋转键数：
  29
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  342
• 氢给体数：
  1
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  Man2Ac3Ac4Ac6Ac(a1-2)Man3Ac4Ac6Ac(a1-2)Man3Ac4Ac6Ac(a)-O-C(NH)CCl3 在 三氟甲磺酸 、 碳酸氢钠 、 硫脲 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 phenyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1-2)-O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1-2)-O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1-3)-2,4-di-O-benzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  A Short, Efficient Synthesis of the Octamannan Residue of High Mannose Type Sugar Chains

  摘要：

  An efficient route for the synthesis of octamannan 1, found in high mannose type sugar chains, is described. To construct octasaccharide 1 by as few synthetic steps as possible, we employed a chemoenzymatic strategy: the enzymatic synthesis of oligosaccharide blocks using glycosidases followed by chemical coupling to form a branched structure. By use of this methodology, many synthetic steps were eliminated and 1 was easily synthesized.

  DOI：

  10.1080/07328309808001897
• 作为产物：
  描述：

  在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 Man2Ac3Ac4Ac6Ac(a1-2)Man3Ac4Ac6Ac(a1-2)Man3Ac4Ac6Ac(a)-O-C(NH)CCl3
  参考文献：
  名称：

  Ito, Yukishige; Kanie, Osamu; Ogawa, Tomoya, Angewandte Chemie, 1996, vol. 108, # 21, p. 2691 - 2693

  摘要：

  DOI：

文献信息

• Rapid assembly of branched mannose oligosaccharides through consecutive regioselective glycosylation: A convergent and efficient strategy
  作者：Bo Meng、Jun Wang、Qianli Wang、Anthony S. Serianni、Qingfeng Pan

  DOI：10.1016/j.tet.2017.05.073

  日期：2017.7

  A convergent and efficient strategy for the synthesis of high-mannose oligosaccharides is described wherein regioselective glycosylations between trichloroacetimidate donors and partially protected acceptors are employed to reduce the number of protection–deprotection steps. Two representative branched mannose oligosaccharides, a mannose heptasaccharide (Man7) and a mannose nonasaccharide (Man9) were

  描述了一种合成高效甘露糖寡糖的策略，其中三氯乙酰亚氨酸酯供体和部分受保护的受体之间的区域选择性糖基化被用于减少保护-去保护步骤的数量。通过（4 + 3）和（5 + 4）糖基化分别构建了两个代表性的分支甘露糖寡糖，甘露糖七糖（Man 7）和甘露糖九糖（Man 9）。这些含有甘露糖的寡糖可通过9个步骤获得，总收率为25％，纯度在60-70 mg范围内大于98％，证明了该策略的有效性。
• Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems
  作者：Alison M. Daines、Ben W. Greatrex、Colin M. Hayman、Sarah M. Hook、Warren T. McBurney、Thomas Rades、Phillip M. Rendle、Ian M. Sims

  DOI：10.1016/j.bmc.2009.05.043

  日期：2009.7

  Immunostimulatory saponin based colloidal antigen delivery systems show promise as adjuvants for subunit vaccines. For this reason, allyl oleanolate was glycosylated at the 3-position using trichloroacetimidate donors to give monodesmodic saponins following deprotection. Bisdesmodic saponins were synthesized by double glycosylation at the 3- and 28-positions of oleanolic acid. When formulated together with cholesterol and phospholipids, ring-like, helical and rod-like nanostructures were formed depending on the saponin concentrations used. As an indication of adjuvant activity, the ability of these formulations, and the saponins by themselves, to induce dendritic cell maturation was measured, but no significant activity was observed. (C) 2009 Elsevier Ltd. All rights reserved.